1,2-Benzenedicarbonitrile
- Formula: C8H4N2
- Molecular weight: 128.1308
- IUPAC Standard InChI: InChI=1S/C8H4N2/c9-5-7-3-1-2-4-8(7)6-10/h1-4H
- IUPAC Standard InChIKey: XQZYPMVTSDWCCE-UHFFFAOYSA-N
- CAS Registry Number: 91-15-6
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: Phthalonitrile; o-Benzenedicarbonitrile; o-Cyanobenzonitrile; o-Dicyanobenzene; Phthalodinitrile; 1,2-Dicyanobenzene; o-Phthalodinitrile; o-PDN; Phthalic acid dinitrile; USAF ND-09; 1,2-Benzodinitrile; 1,2-Benzendikarbonitril; Ftalodinitril; Ftalonitril; o-Benzenedinitrile; NSC 17562
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Phase change data
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 414. | K | N/A | Buckingham and Donaghy, 1982 | BS |
| Tfus | 412.92 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.25 K; TRC |
| Tfus | 413.05 | K | N/A | Witschonke, 1954 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Ttriple | 414.0 | K | N/A | Rabinovich, Nistratov, et al., 1984 | Uncertainty assigned by TRC = 0.2 K; TRC |
| Ttriple | 414.0 | K | N/A | Karyikin, Shvetsova, et al., 1982 | Uncertainty assigned by TRC = 0.1 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 86.9 ± 1.5 | kJ/mol | V | Sato-Toshima, Sakiyama, et al., 1980 | ALS |
| ΔsubH° | 86.9 | kJ/mol | N/A | Sato-Toshima, Sakiyama, et al., 1980 | DRB |
| ΔsubH° | 86.9 ± 1.5 | kJ/mol | GS | Sato-Toshima, Sakiyama, et al., 1980 | AC |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 423. to 425. | 0.013 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 20.000 | 414.0 | Rabinovich, Karyakin, et al., 1984 | DH |
| 20.000 | 414.0 | Karyakin, Shvetsova, et al., 1982 | DH |
| 20.0 | 414.1 | Karyakin, Shvetsova, et al., 1982, 2 | AC |
Entropy of fusion
| ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 48.26 | 414.0 | Rabinovich, Karyakin, et al., 1984 | DH |
| 48.26 | 414.0 | Karyakin, Shvetsova, et al., 1982 | DH |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Witschonke, 1954
Witschonke, C.R.,
Freezing point and purity data for some organic compounds,
Anal. Chem., 1954, 26, 562-4. [all data]
Rabinovich, Nistratov, et al., 1984
Rabinovich, I.B.; Nistratov, V.P.; Babinkov, A.G.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V.,
Thermodynamics of the condensation of o-phthalic acid dinitrile with m-phenylenediamine,
Izv. Akad. Nauk SSSR, 1984, 1984, 779. [all data]
Karyikin, Shvetsova, et al., 1982
Karyikin, N.V.; Shvetsova, K.G.; Dzharimova, E.S.,
Thermodynamic properties of o-phthalic acid dinitrile,
Termodin. Org. Soedin., 1982, 33-37. [all data]
Sato-Toshima, Sakiyama, et al., 1980
Sato-Toshima, T.; Sakiyama, M.; Seki, S.,
Thermochemical estimation of destabilization energies of 1,2-, 1,3-, and 1,4-dicyanobenzenes due to interactions between substituents. Appendix: Dipole moments in solution of the dicyanobenzenes,
Bull. Chem. Soc. Jpn., 1980, 53, 2762-2767. [all data]
Rabinovich, Karyakin, et al., 1984
Rabinovich, I.B.; Karyakin, N.V.; Dzharimova, E.S.; Siling, S.A.; Ponomarev, I.I.; Vinogradova, S.V.,
Thermodynamics of the condensation of o-phthalic acid dinitrile with m-phenylenediamine, Izv. Akad. Nauk SSSR,
Ser. Khim., 1984, (4), 779-787. [all data]
Karyakin, Shvetsova, et al., 1982
Karyakin, N.V.; Shvetsova, K.G.; Dzharimova, E.S.,
Thermodynamic properties of o-phthalic acid dinitrile, 1982, Termodin. [all data]
Karyakin, Shvetsova, et al., 1982, 2
Karyakin, N.V.; Shvetsova, K.G.; Dzharimova, E.S.,
Termodin. Org. Soedin., 1982, 33. [all data]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔsubH° Enthalpy of sublimation at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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